He Loves Me, He Loves Me Not
by YouCouldBeHappy11
Summary: Elena Gilbert is learning the hard way that not everyone gets the man of their dreams, and sometimes, if you're lucky, said man of dreams ends up marrying your best friend. As Elena helps plan the wedding of dream guy and best friend, she meets dream guys brother and things get complicated. Will Elena finally get her happily ever after? And if she does, which brother is her prince?
1. Ties & Almost Kisses

**AN: Hi, babes! Long time no talk, eh? I'm so sorry I've been completely MIA for the past few weeks. I literally _just_ got back from vacation, and that mixed with a severe case of writers block, it's safe to say I wasn't doing a lot of writing. But do not fret! I am back with a new story for you all. But before I get to that, I have a few things I need to talk to you about.**

**First of all, thank you guys so much for the overwhelming response to Nothing's Fair When It Comes To Love. I was so blown away by how many views and wonderful comments you sent my way, that I will admit, I got a little teary-eyed. Thank you again. You don't know how much it means to me. While we're on the subject of NFWICTL, I'll be honest with you guys when I tell you that I had always planned for that to be a one-shot. For me, it was closure. I needed to write out a scene like that so I could get out all my frustrations. I never had any plans for it to become more, I never had a second chapter planned, I didn't even know what the plot would be if I did decide to make it into more, and I think that's why I was having such a hard time writing. I didn't know where to go. So, for now, I'm sticking with my gut and letting that stay as a one-shot. I know a lot of you were looking forward to more chapters, and I'm really really sorry. I just can't find the inspiration for that particular fanfic, and I hope you all can forgive me.  
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**With that being said, I have a TON of inspiration for this new story, and I'm excited for you all to read it. I was watching 27 Dresses the other night when POOF! Damon and Elena popped into my head. I loved the idea of Elena being in love with her boss, and then him falling in love with her sister, and then Elena meeting this guy that she can't stand, but he somehow gets under her skin and they build this friendship/relationship and it's just really drama-filled and angsty. I loved it! If you haven't seen it, I would definitely suggest you rent it sometime. It's super cute. But anyway, I just thought I'd let you all know that He Loves Me, He Loves Me Not is going to be loosely based off of that movie. I am for sure going to change a lot of it and make it my own, but the main idea is the same. Just up front, Elena's sister is now her best friend, and the guy that Elena meets is going to be her boss's brother. Okay, I think that's it! Sorry this AN was so long. :/ I promise next time it won't be!  
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**I hope you enjoy. :)  
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**Oh, and one more thing. I know a lot of you will most likely not like this first chapter, and trust me, it was just as hard for me to write as it probably will be for you to read. I think I barfed in my mouth a little bit with that first scene, tbh, but it's necessary. The next few chapters have a lot of information that you need to know, and yes, that includes Stefan/Elena. Yuck! But keep reading, and I promise, it will get better.  
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**Okay, now I'm really done. Don't forget to review. Love you guys. MWAH 3**

* * *

"Elena, could I see you in my office, please?"

The intercom beeped and Elena's whole body erupted in goosebumps at the sound of his voice. She quickly grabbed her belongings and made her way to his office, not bothering to stop and say hello to the many colleagues she passed on the way. Stefan needed her, and she didn't want to miss a second of being there for him.

"God, I'm pathetic," she groaned silently to herself. She quickly slowed her pace before she was in a full out sprint, and then paused just outside his door. Taking a deep breath, she knocked loudly on the wood.

"Come in," he said, and Elena swore she could hear her heart drumming wildly in her ears at those two measly words.

"You needed to see me?" she asked nervously as she stepped into his office. He was facing away from her, and she couldn't help but stare at his perfectly toned back. Her eyes traveled up and down his body, admiring the way his muscles seemed to be begging for releasement from his tight dress shirt. She definitely wouldn't mind helping him out with that. Stefan turned towards her then, and Elena's whole face flushed red at the thought of being caught ogling her boss. He didn't seem to notice.

"I need your help," he said sheepishly, holding up a red and a blue tie in both hands.

Elena grinned at the sight. She walked further into the spacious room and stopped a few feet in front of him. "Hmm," she said, lightly tapping her index finger against her chin.

"Come on, Lena," he whined. "I need to be at this benefit in five minutes, and I don't know which tie to wear. Red or blue?"

At the sound of the nickname Stefan had given her a year and a half ago, tiny butterflies erupted inside of her stomach. "Blue," she said, trying to keep her voice even and not give away the fact that she felt like a stupid schoolgirl every time she was within 100 feet of him.

Stefan smiled widely at her and tossed the red tie onto the couch. As he fumbled with putting the blue tie successfully around his neck, Elena laughed.

"Here, let me do it," she said, walking the few short feet to where he was standing. As she began to fix his tie, Stefan watched her.

"How are you so good at this?" he asked.

"I've had a lot of practice with putting ties on men," she said, trying to focus her attention on the tie, and not on the way his close proximity was affecting her.

Stefan raised his eyebrows. "Oh?"

Elena blushed profusely, realizing how that must have sounded. "I used to help my Dad and my brother put their ties on," she explained quickly. "My mother could never figure out how to do it." Before Stefan could respond, she changed the subject. "You know, for someone who wears ties so often, you really do suck at this."

Stefan laughed lightly, and the noise was like music to her ears. "I know," he said. "Thank God I have you to help me."

"That's true. I mean, what would you do without me?" she teased, finishing up the tie. She smoothed out his shirt and then looked up at him, surprised to find him staring at her intensely.

Their eyes met, and Elena was sure she was about to melt into a puddle on the floor. She wanted to say something, but no words would come out of her mouth. They gazed at each other for what felt like hours, until Elena couldn't take it anymore. She felt herself slowly inch forward, and as hard as she tried, she couldn't get her body to stop. What the hell was she doing? She was going to look like such an idiot when Stefan pushed her away, and she wasn't sure she was capable of dealing with that kind of humiliation. She anxiously waited for him to say or do something, but he didn't move. He didn't jump away in disgust. He didn't clear his throat and ask her what the hell she was doing. He didn't do so much as bat an eyelash, and Elena sucked in a nervous breath. That was a good thing, right? He was still standing right in front of her, and it could have been the lack of oxygen getting to her brain, but she was almost positive that he was leaning towards her too.

"Oh my god," she thought wildly to herself. Was this it? Was she finally, after three agonizing years of pining over him, going to get to kiss Stefan? Was this going to be the beginning of it all? Was she really about to feel his lips on her. . .

There was a loud knock on the door and Elena jerked backwards, fumbling over herself like the idiot she was.

"Stefan, your car is waiting downstairs," Bonnie, his secretary and Elena's best friend, said, peeking her head through the doorway. She looked between Stefan and Elena and raised her eyebrows questioningly. Elena, who was still trying to catch her breath and get her face to return to a shade other than bright red, looked to the floor as Stefan walked to his coat rack.

Slipping on his jacket, he tightly smiled at his secretary. "Thanks, Bonnie. I'll be down in a minute."

She shot Elena a knowing glance before nodding at her boss and shutting his door.

Stefan immediately looked to Elena, and before he could say anything, she briskly walked to the door. "So, um . . . have a good time at your benefit tonight," she said lamely, wishing the floorboards would open up and eat her so she didn't have to deal with Stefan's rejection.

"Elena," he murmured, causing her to turn and look at him expectantly. He stared at her for a beat, not saying a word, and then Elena turned back around, humiliated. There was no way she was going to stick around and hear him say that he wasn't interested in her in that way, or that he was seeing someone, or that he was confused. She didn't want to hear him say anything, not in that moment, so she plastered on her best fake smile and shot it Stefan's way.

"I'll see you later," she said before rushing out the door, leaving a very speechless Stefan Salvatore behind her.

As Elena silently walked back to her office, she wanted nothing more than to go home, crawl into a tiny ball, and cry. She felt so stupid. What the hell had she been thinking back there? There was no way a guy like Stefan would ever want to be with a girl like her, let alone kiss her in the middle of his office, where anyone in the entire building could walk through the doors at any given moment. God, she wanted to die. She could only imagine what Stefan must have been thinking, how he would probably laugh about it with his friends later on. "Hey guys! Guess what one of my employees tried to do today? Kiss me! She actually tried to kiss me. You should have been there, it was too great." She could hear it now, and it made her stomach twist in knots. She was going to be sick.

She quickly started making her way to the bathroom, but a voice from behind made her stop.

"Oh, don't think you're getting away from me that easily, Elena Gilbert."

Elena internally groaned. Bonnie. With all of her thoughts revolving around her humiliation, she had somehow forgotten that Bonnie had walked in on her and Stefan just as they were about to kiss. Well, just as Elena was about to kiss him and make a total fool out of herself. Fuck.

She slowly turned to face her best friend, a look of pure guiltiness on her face. She opened her mouth to speak, but Bonnie cut her off.

"Be a little more obvious, Elena. You look like you're taking the walk of shame," she said, her eyes growing wide. "Oh shit, he kissed you, didn't he? Oh my god!" she squealed. "How was it? Is he as good of a kisser as he looks? Give me all the details!"

"Shh," Elena hissed, forcefully grabbing Bonnie's arm and dragging her into the bathroom. She checked under each stall to make sure the coast was clear, and then looked back to Bonnie who was still rambling on, completely oblivious.

". . . And at work too! I didn't think you had it in you, Gilbert, but it looks like some of my badass-ness has worn off on you after all. I feel like a proud mother." Bonnie wiped at her eyes as if she was crying, and Elena couldn't help but roll hers.

"Bonnie," she said quietly, causing her best friend to close her mouth and look at her. "Nothing happened . . . with Stefan." Elena's throat had become painfully dry, and her voice shook with each word that she said, but she continued anyway. "I was helping him with his tie, like I always do before he goes to an event, and for some reason it felt . . . different. Like something big was about to happen. We were looking into each other's eyes, and before I knew what was happening, I was leaning in, trying to kiss him. And for the first time, I thought that just maybe he wanted to kiss me too. But then you interrupted us, and after you left he didn't say anything. He just stared at me like I was some three-headed monster who had tried to eat his face off. God, I feel so stupid," she wailed, throwing herself into Bonnie's open arms.

"I'm so sorry," Bonnie whispered, rubbing soothing circles onto her best friends back. "But you are not stupid, Elena. Stefan is. If he was smart, he would have locked the door after I left, grabbed your face, and kissed the fucking shit out of you. I would have."

Elena smiled through the tears that were silently rolling down her face. "Thanks, Bon," she said. "I just feel like such an idiot. I have no idea what I was even thinking, and now he's probably off laughing at me." Elena buried her face in Bonnie's neck as she thought of the look Stefan had given her on her way out.

"Hey now," Bonnie said, grabbing Elena's shoulders and pulling her back. "Stefan is not laughing at you. He's not that kind of person, and you know it. As for the rest of it, all I can say is: his loss. He had his chance and he blew it. If he can't see what an amazing person you are, then he's seriously not worth your time."

Elena ran her fingers through her hair and sighed. "I know you're right, but. . ."

"But nothing. You've been in love with this guy for three years, Elena, and he's never once made any sort of move to get closer to you. It's not fair. You don't deserve that."

"But he's Stefan, Bonnie!" Elena exclaimed, throwing her hands up in defeat. "No matter what he does or says, and no matter how hard I try, I can't get over him."

"I know," Bonnie said comfortingly. "I just hate to see you this way."

Elena nodded. She hated_ feeling_ this way. It was exhausting, having feelings for someone who didn't feel the same way, but she would put on her best brave face and get over it. It's not like this was the first time she had cried over Stefan, and it certainly wouldn't be the last. "It's fine, Bon. I'm okay, really," she said, grabbing her friend into a tight hug. "Thanks for listening to me and my pathetic life. I don't know what I'd do without you."

Bonnie smiled. "You know I'll always be there for you, E. But you're not pathetic, okay?"

She most definitely felt pathetic, but Elena nodded and gave her friend another squeeze before pulling away. "I think I'm gonna call it a day. I don't feel too well, so I think I'm gonna head home early. I'll call you later?"

"Of course. I'll talk to you soon."

Elena slightly smiled before heading towards the door. "Oh, and E?" Bonnie said, causing Elena to turn back around. "Remember what I said."

* * *

It had been six hours since Elena had returned home from work, thrown on her pajamas, and gotten into bed. As she lay on her plush mattress, a carton of chinese food to her left, the remote control to her right, she realized just how wrong Bonnie truly was. She was the epitome of pathetic.

She knew that tomorrow she would have to get up, get dressed, and deal with the real world, but for now, she was completely content with never leaving her bed.

There was suddenly a knock on the door, and Elena buried her face beneath a pillow. "Go away," she said, her voice muffled by the fabric. The knocking continued and Elena groaned. She was in no mood to see anyone tonight, and she silently prayed that whoever was on the other side of the door would take a hint and go away. After five more minutes of persistent knocking, she took a deep breath and threw her legs over the edge of bed, slowly making her way towards the door. "All right, I'm coming," she shouted.

As she reached the front of her apartment, she wondered who in the hell would be coming to see her at 10PM on a Tuesday. She grabbed the door handle and slowly opened it. Her mouth dropped wide open at the person standing in front of her. "Caroline?


	2. I've Got A Future Husband to Meet

**AN: Hi guys! Just dropping by to say thank you so much for being so enthusiastic about this new story. I'm really excited for you to see where I plan to take it. :) I try to reply to every comment I get, so make sure you leave me one with your thoughts and opinions on things about the plot/characters/etc. Feedback makes my day!  
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**I think that's about it! I told you this AN wouldn't be as long as the last one, didn't I? ;) So without further ado, I present to you Chapter Two of He Loves Me, He Loves Me Not. I really hope you enjoy, and don't forget to tell me what you think! We'll start back right where we left off. .  
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* * *

"Surprise!" the young blonde squealed, throwing the suitcase gripped tightly in her hand to the floor as she swept Elena into a hug.

Elena stood still, her mouth hung open in shock. "Caroline, what are you doing here?" she asked.

Caroline released Elena from the hug and frowned. "I'm here to see my best friend," she said, as if it was the most obvious thing in the world. "You know, the one who hasn't seen me in three years?"

Elena smiled tightly at the girl standing before her and decided that she wouldn't really call them 'best friends.' She had known Caroline Forbes practically her entire life, and although they had been virtually inseparable during high school, the minute they got to college everything had changed. Caroline was the loud, wild one that every guy wanted, and Elena was the quiet one, the who would rather stay in and study than go out and party. Thinking back, she couldn't even remember a time during those long four years where they hadn't argued over anything and everything. Choosing to ignore this minor detail for the sake of not starting things off on the wrong foot, Elena said, "So you're back from Paris?"

Caroline huffed impatiently, tapping her high-heeled boot loudly on the floor. "Yes, silly, I'm back from Paris. I mean, helloooo, I'm standing right in front you!"

Elena internally rolled her eyes. "What happened to Klaus? Last time we talked you said you guys had moved in together. . ." Elena paused, craning her neck to inspect the hallway. "He didn't come with you, did he?" Having Caroline as a house guest was going to be hard enough, but if she had to deal with Caroline AND her European douche-bag of a boyfriend, Elena would most likely be admitted into a psychiatric ward within the month.

"Don't worry, he's not with me," Caroline said, shooting her friend the biggest smile she had ever seen.

"Did something happen?" the brunette asked skeptically. This definitely wouldn't be the first time Caroline had come running home after a breakup. The girl went through guys like water, and she was known for being overly dramatic.

"Yeah, I finally dumped his sorry ass," she said, shrugging her shoulders in indifference. As Elena opened her mouth to reply, Caroline quickly raised a hand to cut her off. "Can we talk about this later? I was just on a plane for eight hours, and I could really use a shower. And a large bottle of wine." She grinned sheepishly, picking her suitcase up from the floor.

Elena shuffled on her feet slightly, bringing the open door of her apartment closed by an inch. "How long are you going to be in town?" she asked, angling her body so Caroline couldn't peer inside.

Caroline narrowed her eyes as she sucked in a deep breath. "You know, if I didn't know any better, I'd think that you weren't excited to see me." Elena smiled weakly and shook her head no. The blonde waited for her to say or do more, and when she didn't, she let out a groan of annoyance. "Fine. I'm not sure how long I'll be in town, but I promise I won't stay too long. I can tell I am not welcome here."

Elena sighed. There was the dependable and always overly emotional Caroline she knew and tolerated. "Of course you're welcome here, Care," Elena said, stepping aside so she could let her through the door.

"Yay!" Caroline squealed in excitement. She made her into the apartment, pausing to throw her suitcase carelessly onto the kitchen table. As she inspected the tiny place Elena called home, she noticed a couch a few feet away. "Thank god," she said to herself, making her way to the piece of furniture and plopping her body down onto the plush fabric. She looked up to Elena, who was standing against the wall, her arms crossed tightly over her chest, and a smile broke out on her face. "This is going to be so much fun!" She cooed, clapping her hands wildly. "It'll be just like college."

Elena's stomach dropped. Oh god, she hoped not.

* * *

"Caroline, hurry up!" Elena screamed through the bathroom door, pounding her fists as loudly as she could against the hard wood. There was no response, and Elena was almost positive that at any second she was going to lose her mind. "Caroline, we were supposed to be there FIFTEEN minutes ago, and like I've told you a thousand times, this is a work event. I can't afford to be late!"

The bathroom door swung open suddenly, revealing a perfectly made up Caroline. "All ready," she smiled.

Elena threw up her hands in aggravation. "I swear I'm going to kill you one of these days," she said, rolling her eyes as Caroline stuck out her tongue.

"Lena, don't worry. This 'work event' is at a bar. I seriously doubt they are keeping tabs on when their employees show up." Caroline brushed past Elena and made her way towards the front of the apartment, stopping momentarily to check herself out in the floor length mirror hanging against the wall. Elena followed behind her, her movements laced with hostility.

"That's not the point, Care," she said as they reached the kitchen. "The point is I made a commitment to my boss that I'd be there at eight, and it's now," she looked at the watch on her wrist, "8:20! And then with the traffic we probably won't end up even getting there until 8:45." She anxiously ran a shaky hand through her hair.

Caroline watched her in amusement. "Elena, you need to chill," she said, placing a hand on her shoulder. "Why are you so worked up over this?"

Elena sucked in a deep breath. There was no way she was going to tell Caroline that the reason she was so 'worked up' was due to the fact that this would be the first time she had seen Stefan since the almost kiss incident, and she was completely scared to death. She had no idea what she was going to say to him, and it really pissed her off that even after his rejection, her heart was still thumping wildly in her chest at the idea of seeing him.

"Earth to Elena!" Caroline said, interrupting her thoughts. "Are you even listening to me?"

"Of course I am," she snapped, turning to face the blonde. She closed her eyes for a brief second and tried to calm herself down. She knew she was being a bitch to Caroline, and although she _was_ the reason they were late, Elena knew that she didn't deserve this kind of treatment. She was taking out her frustrations on her friend because she was the closet one around, and it wasn't fair. "Look, Caroline, I'm sorry. I didn't mean to yell at you back there. I just really need to get to this bar as soon as possible, okay?"

Caroline simply nodded her head. "Okay. Let's go."

Elena smiled to herself in triumph. Finally!

Twenty minutes later, Elena and Caroline pulled up to The Grill, the restaurant slash bar that everyone in the small town of Mystic Falls had been to at one point or another in their lifetime. It was the only real form of entertainment the town offered, and Elena knew firsthand that the bartenders were never really thorough with checking I.D.s, thus, making it a very popular establishment with high school students. Tonight, however, Stefan had rented out the entire Grill for a 'celebration,' as he called it. The firm had just landed a huge client, and the whole staff had been invited to kick back, relax, and have some fun.

As Elena parked the car and walked towards the entrance, Caroline in step beside her, she wondered just how much fun she was going to be having tonight. Knowing Caroline, she was most likely going to ditch her within the first twenty minutes, having found some random guy to hook up with. It had been like this all throughout college, and Elena didn't expect that to change now, just because they were a few years older. Normally, this wouldn't have bothered her, but tonight she was feeling vulnerable, and there was no way she was going to get trapped into talking to Stefan alone. "Hey, Care?" she asked, pausing right outside the door to the bar.

Caroline turned her head and looked at Elena questioningly. "Yeah?"

"Let's stick together tonight, okay?" she paused, contemplating what to say. "There's just . . . there's just some real skeeves that work with me, and I'm not in the mood to have to talk to them all night as they try to discreetly look down my shirt."

Caroline giggled. "You got it." She grabbed the door handle and noticed Elena's apprehensive stare. "You sure you're okay? I promise I won't let any dirt bag get too close to you."

Elena laughed lightly as Caroline stuck up both her fists and punched the air. She took one last deep breath before nodding her head. "I'm fine. Let's go."

Caroline threw her arm around Elena's shoulder and howled. "It's gonna be a good night, Gilbert. I can feel it!"

As they entered The Grill, Elena was overwhelmed with the amount of people that were currently occupying the fairly small building. It seemed as if every inch of the bar was inhabited by a body, and she had never seen it so packed. Caroline winked at her, as if to further illustrate her prediction, and Elena rolled her eyes. She pointed towards the bar counter and Caroline's eyes lit up with the prospect of alcohol.

"Yes, please," she said as they quickly walked to the counter. As a group of men Elena recognized as co-workers from the third floor ordered their drinks, the two girls stood to the side, surveying the room. Elena searched for Stefan, but thankfully, he was no where to be found. She only prayed that he would stay like that for the rest of the night, or until she had come up with a good enough excuse as to what the hell had happened in his office two days ago.

Elena's thoughts were interrupted by Caroline's voice in her ear. "Okay, don't make it obvious, but check out the bartender behind you."

"What? Why?" she asked, whipping her head to the side.

"I said don't make it obvious!" Caroline hissed, yanking Elena's body forward.

She yelped in surprise and quickly pulled her arm out of Caroline's grasp. "What the hell was that?"

Caroline huffed impatiently. "Just check out the bartender, okay? But this time, try not to be so fucking obvious!"

Elena crossed her arms tightly across her chest. "Fine," she said through clenched teeth. She slowly, and discreetly, turned her head until she had a clear view of the man tending the bar, her eyes widening as she took in his messy raven colored hair, his dark black t-shirt that could barely contain his bulging muscles, and his eyes that were so clear and blue, they looked like the sky. "Wow," she breathed, turning back towards a giggling Caroline.

"I know, right?" she exclaimed. "I bet he's a model who works here part time for some extra cash. No way a man that gorgeous isn't getting paid for it. That would be such a crime to the world."

Elena hit Caroline half-heartedly on the arm. "Shut up," she said, laughing despite herself. Although Caroline was right, he certainly was gorgeous, the bartender wasn't Stefan, and she doubted he ever would be. "Come on, let's go get a closer look." She grabbed her arm and pulled her towards the front of the counter. Caroline eagerly followed.

As they approached the bartender, his mouth quirked up into a half smile, and Caroline pinched Elena's arm in excitement. Elena pinched her back. "Calm down," she whispered harshly. "And don't pinch me again."

Caroline shrugged, sliding into an open seat in front of the man. She smiled flirtatiously at him, and Elena had to keep herself from snorting. And Caroline called her obvious.

"What can I get you, ladies?" the bartender said smoothly as Elena took the seat directly beside Caroline.

"Well, I would just love a Sex On The Beach," she said, throwing him her 'come hither' look, and this time Elena actually did snort. Caroline glared at her briefly before turning back to the bartender.

"One Sex On The Beach coming up," he said. "And what about for you?" He turned to face Elena now, and she couldn't help but notice that his eyes were even bluer up close. "Did you want something to drink?" he asked when she didn't respond.

"Oh, um . . . nothing for me right now," she said, her cheeks turning slightly pink at the realization that he had probably noticed her zoning out on his eyes. She was such an idiot.

The bartender nodded his head and went to work on Caroline's drink. As soon as his back was turned, Elena swiveled her seat so she was looking out into the room.

"What a beautiful piece of man he is," Caroline whispered, following Elena's lead and turning to face the crowd.

Elena nodded, and as she opened her mouth to respond, Caroline grabbed her arm wildly. "Elena, who is that?" she said, her voice almost breathless.

Elena looked around the overcrowded bar. "Who is who?" she asked, not having any idea who her friend was talking about.

The blonde raised a shaking hand and pointed to a man about ten feet away. "Who is _**that**_?"

Elena's eyes followed Caroline's finger and her heart immediately dropped straight into her stomach as she saw who her friend was pointing at. Stefan.

"Umm." Elena was rendered speechless. "Well. . ."

"Elena, do you know who that is?" Caroline asked, her hand still poised in the air.

What the fuck was Elena supposed to say? Well, now that you mention it, Caroline, that's the man I have been desperately in love with for the past three years?

"Elena," Caroline whined, growing impatient.

"That's my boss," she said quietly, trying to swallow the lump in her throat.

Caroline's eyes grew wide. "That's your boss?" Elena nodded. "Oh my god, no wonder you love going to work! He is the most beautiful creature I have ever laid eyes on."

Elena's heart hammered erratically in her chest. Oh no. Oh no, oh no, oh no. Elena knew from experience that when Caroline put her mind to something, she didn't stop until she got it, and based on the way she was devouring Stefan with her eyes, it was safe to say Elena knew who her next target was going to be. "I thought the bartender was the most beautiful creature you'd ever seen?" she said loudly. "Remember him? He's standing right behind us? Come on, let's turn around and remind ourselves of how gorgeous he is!" Elena tried desperately to turn Caroline back towards the counter, but she wouldn't budge.

"The bartender doesn't even come close to your boss," she said matter of factly.

Elena laughed nervously. "I don't think so, Care. The bartender is honestly way cuter than Stefan."

"His name is Stefan?" Caroline asked eagerly. "Oh my god, that is so hot! Do you think I should go talk to him?"

"No!" Elena screamed, clamping her hand firmly over her mouth before she could said anything else.

Caroline stared at her intensely. "Why not? Is he a bad guy or something?"

Elena shook her head no. Stefan was the farthest thing from a bad guy, and even though she desperately wanted Caroline to stay as far away from him as possible, there was no way she could lie and say he was anything short of amazing. "No, that's not it. Stefan is a really great guy," she began.

Caroline quickly cut her off. "So I have your blessing? Yay!" She squealed. "Thank you so much, Elena. I'm gonna go talk to him now."

"No, you can't!" Elena said frantically, yanking Caroline back to the bar before she could take a single step forward.

"Why not?" Caroline's face was a mix between curiosity and agitation, and Elena knew that she was pissing her off, but she just couldn't let Caroline get her hands on Stefan. She couldn't.

"Because . . . because you . . . um . . . because you promised me you wouldn't leave me alone tonight!" Yeah, that was it. Elena smiled triumphantly to herself. Only a cold, heartless person would back down on a promise.

Caroline rolled her eyes and gave her a pointed look. "Elena, you'll be fine, okay? If any guys try to hit on you just kick them in the balls."

Elena's mouth dropped open in shock. "But you promised," she sputtered.

Choosing to ignore her, Caroline flipped her hair and adjusted her dress. "Now if you'll excuse me, I have a future husband to meet. Wish me luck!" She wrapped Elena in a tight embrace before scurrying towards the dance floor where Stefan stood, stuck in what looked like a pretty deep conversation with the 90 year old janitor.

Elena helplessly watched as Stefan's face lit up at the sight of Caroline, and she silently prayed that he was only just grateful for the interruption.

She knew that realistically she had nothing to worry about. There was no way Stefan and Caroline could hit it off. They were like fire and water - the complete opposites of each other. Caroline was the carefree girl that only worried about which mascara to use, and Stefan was 100% about his work. Caroline didn't even have a job, for crying out loud!

She let out a shaky breath. There was definitely no way the two of them would ever become more than some random people who had met at a bar, and Elena tried to convince herself that she had nothing to worry about.

But as she watched her best friend and the love of her life slowly start to sway to the music together, a knot of fear started growing deep within her stomach. She turned back towards the bar and signaled over the bartender. "I'm gonna need that drink now," she said.

* * *

**P.S.: That bartender seems pretty cool, doesn't he? ;)**


	3. Prove It

**She's baaaaaaaaaaaack! **  
**And to make up for being completely MIA for the past 20 years, she comes bearing gifts.**  
**Want to know what your gift is?! Read chapter three and you'll find out.** **;)**  
**(SPOILER ALERT: it's Delena sexual tension. Shh!)  
**

* * *

Elena slipped into the chair silently, her eyes searching the length of the bar for the man she was looking for. A small smile broke out on her lips as their eyes locked, and she quickly looked down, a small blush forming on her cheeks.

"This is the fifth night in a row you've been here, Gilbert," he said, coming to stand directly before her. "I'm beginning to think you might be an alcoholic. That or you're obsessed with me." He smirked wildly at her as an eyebrow rose slightly. "Wouldn't be the first time."

Elena rolled her eyes towards the ceiling. "Damn. You caught me. I just can't seem to resist your overwhelming modesty. Tell me, how do you do it?"

The dark haired bartender snorted. "Your sarcasm never ceases to amaze me," he mumbled, his arms coming to rest against the edge of the counter.

"Thanks," she replied cheekily, trying her best not to stare at the way his black t-shirt accentuated his biceps perfectly. "Beer?" she asked instead, her eyes lighting up noticeably at the idea of alcohol.

He nodded his head slightly as he walked to the other end of the bar and grabbed a bottle of the brown liquid. He set it down in front of her and watched as she greedily swallowed down half of it. "Rough day?" he asked lightly.

Elena closed her eyes as memories of the day flitted through her mind painfully. "You have no idea," she mumbled quietly.

_"Don't you think you're moving kind of fast?" she asked nervously, her fingers running through her dark hair as she stared intensely at her best friend. _

_ Caroline stood in front of the floor length mirror, carefully inspecting the gold dress that hugged her curves perfectly, and shook her head. Her eyes met Elena's in the mirror, and she quickly turned around to face her. "I know it seems like we're moving really fast," she paused, "but I think I'm falling in love with him."_

_ Elena felt her heart completely stop as she stared open-mouthed at the blonde. "You're what?" she asked almost inaudibly as she tried to push away the panic that was quickly rising in her body. _

_ Caroline smiled widely as she bounced slightly on her toes. "I think I'm in love with Stefan," she beamed._

_ The room was spinning and Elena had to clutch tightly at the blankets surrounding her in order to stay up right. "But, Care, you've only known him for a couple of weeks."_

_ She sat on the edge of the bed and grabbed Elena's hands. "I know! Isn't it amazing?"_

_ Elena struggled to breathe. Caroline was in love. With Stefan. _**Her**_ Stefan. The man she had been completely infatuated with for the past three years Stefan. This can't be happening, she thought wildly to herself. It had only been a month since the two had met at the Grill and started dating. There was no way they were already in love._

_ "How can you be in love with him? You barely know him," she said loudly, yanking her hands out of the blonde's grasp. _

_ Caroline folded her arms around her chest defensively. "Of course I know him. I've known him since the minute I laid eyes on him. It was love at first sight, Elena."_

_ The brunette had to physically fight the urge to start hysterically laughing. Love at first sight? Between Caroline and Stefan? Not a chance in hell. "Are you hearing yourself? Love at first sight? I know you think you love Stefan, but I'm not sure you do."_

_ Caroline jumped off the bed hastily. "Oh yeah? And what do you know about being love? You've been single for years, Elena, and I don't see you out there trying to do anything about it," she yelled fiercely. _

_ "That's right because you know everything about love," Elena said sarcastically, throwing her hands in the air. "You go through guys quicker than normal people go through mascara."_

_ Caroline gasped. "Take that back," she screamed._

_ Elena rolled her eyes so hard she thought she was going to go blind. What were they, twelve? "I'm not taking anything back," she spit harshly. "You can't commit for shit, Caroline, and you think you love Stefan, but you don't." _

_ The words were meant to hurt her best friend, but Elena found herself desperately clinging to them instead. She needed them to be true. They _**had**_ to be true. Watching Stefan and Caroline be together for the past thirty days had been the hardest thing she had ever had to experience, and she wasn't sure how much longer she'd be able to take it. Every time she walked into the kitchen and saw them making out, every time she was forced to listen to Caroline giggle loudly at something Stefan had said, every time they smiled at each other when they thought no one was looking, a piece of Elena's heart broke off, and she worried that by the end of their relationship, there would be nothing left of it. _

_ "You're wrong!" Caroline bellowed, snapping Elena's attention back to the fiery blonde that was now pulling on her shoes. "I love Stefan, and Stefan loves me," she shrugged her shoulders confidently. "Believe whatever you want, but what we have is real." _

_ Elena opened her mouth to protest, but Caroline held up a hand. "Save it." She grabbed her purse from the bedside table and walked to the door. "Now if you'll excuse me, my boyfriend should be here any minute to take me out to dinner, because he _**loves **_me." As she started to walk away, she changed her mind suddenly and turned back towards Elena who was sitting speechless on the bed. "Have a good night being alone," she said, slamming the door on her way out. _

"You want to talk about it?" he asked, his voice soft and soothing, successfully bringing Elena back to reality. Her eyes popped open and she stared at the man before her. If there was one good thing that had come out of Stefan and Caroline's relationship, it was him.

She had started coming to the Grill on a regular basis about three days after the two had started dating. Although Stefan had a house all to himself, and Caroline had a roommate, the couple insisted on spending every waking minute together crammed into Elena's tiny apartment, and that was something she just couldn't deal with. After hearing them having sex for the second night in a row, Elena ran to the bathroom, threw up, and then drove to the Grill, the promise of getting thoroughly plastered and forgetting all about how cruel her life was, too good to pass up.

She hadn't even remembered the dark haired bartender that Caroline had pointed out to her until she was completely hammered and he had come to tell her the bar was closing. He laughed as she stumbled out of the bar, and the sound had made her insides feel like jello. She blamed it on the twelve tequila shots she had consumed that night.

She returned the next day, the sight of Caroline and Stefan curled up on the couch warranting copious amounts of vodka, and she had seen him again. This time they had actually managed a full conversation before she was too drunk to form words, and Elena had come to the conclusion that to go along with his breathtakingly good looks, he was also charming and witty, something that both annoyed and excited her.

His name was Damon, and he had just moved back to Mystic Falls after ten years of being away. He worked at the bar full time, his favorite color was black (obviously), and he had one younger brother. Talking to Damon had been good for Elena, and she soon found herself at the Grill every night, not only to escape the torture she called her life, but also to be around him.

She was still completely in love with Stefan, and with the way things were going, she thought she always would be, but Damon made her laugh, and if her heart was dead set on a man she could never have, she might as well give her brain something nice to look at.

"I got into a fight with my best friend," she said, looking up at him and smiling slightly at the confusion she saw in his eyes. "Over a guy."

Damon raised his eyebrows toward the ceiling as he shook his head slowly. "How very junior high of you," he said, a smirk gracing his lips.

She narrowed her eyes. "No, not junior high at all. She's been dating this guy for a month and she says she's in love with him. She's being an idiot." Elena took a sip of her beer and watched Damon as he tried to stifle a grin. "Is something funny?" she asked hotly.

He quickly nodded his head no before his face became serious. "You're right, this doesn't sound childish at all." The words had barely left his mouth before he started laughing loudly.

Elena groaned. "You're a jerk," she said, grabbing the purse from beside her as she got up to leave. Yes, he was handsome and witty and charming, but when Damon really put his mind to it, he could be the most aggravating person she had ever met.

He grabbed her arm before she could turn away and smiled sheepishly. "You're right. It's not funny, and I'm sorry I laughed at your very important friend drama. It won't happen again." He pulled her back to her seat and leaned forward. "If you stay and tell me what happened, I'll give you more beer," he sing-songed, his face only inches from hers.

A smile broke out on her lips and she sighed dramatically. "Fine, I guess I can stay. But only for the beer."

"You wound me," he said lightly, a hand going to his chest as she giggled. He grabbed a brand new beer and set it down in front of her. "So, as you were saying, your friend is an idiot for falling in love with this guy after a month."

Elena shook her head no. "She's not actually in love with him, she just thinks she is."

Damon cocked his head to the side and raised an eyebrow. "How can you be so sure?"

"Because I know Caroline. She's definitely not the falling in love type," she murmured, running her finger along the rim of the bottle. Images of Stefan were now running wildly through her mind, and she had to physically shake her head to make them stop. "And I also know the guy that she's dating. There's no way the two of them are in love."

Damon waited a beat before he opened his mouth to speak. "So, how long did you date him for?"

Elena's mouth dropped open almost comically. "What?" she screeched loudly, her eyes widening as her heart pounded erratically in her chest.

"This guy," he said, eyeing her closely. "You dated him, right?"

She rubbed her now sweaty palms against her jeans. "I don't know what you're talking about," she stuttered meekly. "I never dated him."

Damon snorted. "Come on, Elena, it's pretty obvious you have feelings for this guy. Why else would you be so worked up over the fact that he's in love with your friend?"

"He is NOT in love with my friend," she answered quickly, mentally slapping herself in the face as soon as the words left her mouth. Damon gave her a look that said he knew he was right, and she took a deep breath.

"I never dated him," she repeated as calmly as she could.

He nodded his head in understanding. "So, how long have you been in love with him then?"

Elena groaned loudly as she threw her head in her hands. "Am I that obvious?" she wailed.

Damon shrugged. "Maybe." He grabbed a rag from below the bar and began wiping the counter. "So, how long?"

"Three years?" she whispered from between her fingers, praying that if she answered the question he would drop the conversation.

"Three years?" Elena nodded her head. "But I thought you said your friend only started dating him a month ago."

"She did."

"Your friend started dating him _after_ she knew how you felt?" He shook his head in disgust. "That's pretty fucked up, Elena. You might want to reconsider who you call your best friend."

She lifted her head slightly, only to throw it back into her hands after catching a glimpse of his face. "She doesn't know that I'm in love with him," she whispered meekly.

Damon's eyes widened as he cocked his head in confusion. "Isn't that something a chick would usually tell another chick? Especially if she was your best friend?" he asked.

If the situation hadn't been so completely and utterly screwed up, she might have laughed. "It's complicated," she supplied lamely.

"I don't care how complicated it is. That guy is a complete dick for going after your friend, even if she didn't know how you felt."

Elena shook her head profusely. "No, Damon, that's the thing. He's not a bad guy at all. He's amazing."

Damon scoffed loudly. "No 'amazing' guy goes after a girl's best friend when he knows she's in love with him."

Elena sucked in a deep breath. There was no way she was going to tell him that Stefan didn't know about her feelings either. She was humiliated, and she desperately wanted to leave the Grill and never come back.

"Seriously, what did this guy tell you when he started dating your friend? 'Sorry that you're in love with me, but I think I'm going to start banging your best friend instead?'" Damon folded his arms across his chest, and Elena felt like she had been slapped in the face.

"No, he did not tell me he was going to start banging her," she seethed, her words laced with venom.

"Then what did he say?" he asked again, his voice filled with just as much heat as hers that it made her angry. This was absolutely none of his business, and she was pissed that she had even allowed herself to be put in this situation.

"Drop it, Damon. It doesn't matter." Her eyes met his challengingly and a shot of heat ran up her spine.

"What did he say, Elena?"

"Nothing," she said harshly, tilting her chin defiantly, daring him to ask again.

He lowered his head towards hers, invading her personal space and then some. Their eyes locked and she could feel the tension rolling between them like a tidal wave. "Elena, what did he say?"

"He didn't say anything."

Damon snorted harshly and Elena could feel his breath on her face. "Bullshit. What did he say?"

"Stop it," she yelled in exasperation. She could feel herself close to the edge, the anger she had been feeling towards Stefan and Caroline now mixed with the anger she felt towards the smug bartender who was currently making her see red.

"Answer the god damn question. What did he say?" he yelled back, his voice reflecting just as much anger as Elena was feeling.

"He doesn't know, okay? He doesn't know," she screamed, her hands flying from their position on the bar to push Damon backwards.

He stumbled only slightly, caught off guard by her tiny hands, before catching himself and straightening himself out. His brows were so furrowed she could barely see his eyes, and a look of pure bewilderment was plastered on his face. "He doesn't _know_?"

Elena clenched her jaw almost painfully. "That's what I just said."

"Have you thought about, oh I don't know, maybe telling him?" he asked sarcastically, throwing his hands in the air as if it was the most obvious question in the world.

Elena's entire body shook as she tried to suck in a breath, her anger so overwhelming she thought she might explode. "It's not like I could make it anymore obvious!" she cried. "I practically try to jump his bones every time he's within 100 feet of me, and I act like such a love struck idiot any time we talk that you'd have to be completely oblivious to not see how I feel."

Damon shook his head hurriedly. "You wanna know what I think? I think you're afraid."

"I'm afraid?" she yelped, her voice cracking as her emotions spiraled out of control. "You don't even know me!"

"Why else would you be sitting around, wallowing in self pity when you've had three years to tell him how you feel?" He scoffed in disgust. "I don't know about you, but that definitely sounds like someone who is afraid."

Elena closed her eyes tightly as she grabbed the bridge of her nose with her thumb and forefinger. "I am not afraid," she said through deep breaths. "It's just . . . it's complicated."

Damon stared at her silently before grabbing the beer from in front of her and throwing it in the trash. He wiped down the counter for a second time, and Elena realized that somehow they had become the only two people in the bar. She glanced at the clock on the wall, and her brows furrowed in confusion. What was he doing? It was only 11:30. The lights went off suddenly, and she looked around, finding his silhouette in the darkness. "What are you . . .?"

"Get up," he said, his voice low. Elena opened her mouth to protest, but he quickly cut her off. "You can make up all the excuses you want, Elena, but you're scared and you know it." He walked towards the door and stood against it. "So get up, and get out of my bar."

Her mouth opened and closed like a fish. "You're kicking me out?" she asked wildly, her voice laced with genuine shock. "What the hell?"

"Sorry, I don't allow cowards to sit at my bar after midnight," he said softly, challengingly.

Elena propelled herself forward until she was standing directly before him, her entire body vibrating with rage. "You do not get to call me that," she spat venomously. "I am NOT a coward."

Damon smirked as he nodded his head lightly. "Okay. Prove it."

She threw her hands in the air in exasperation. "What are you talking about? Prove what?"

"Prove to me that you're not a coward. Go tell this guy how you feel."

Elena's heart plummeted to the floor, and a wave of nausea rolled through her body. "This isn't a game, Damon. I can't just go tell him how I feel. He's dating my best friend!"

Damon shrugged carelessly. "All right, then don't. Be a coward."

"Stop calling me that," she seethed through clenched teeth, her fingers curling into fists at her sides as she tried to stop herself from slapping him across the face.

"I'll stop calling you a coward when you stop acting like one," he shot back fiercely. "Tell him how you feel."

"I can't," she cried, pressing the heel of her palm tightly against her forehead. He didn't understand.

"Yes, you can."

"No, I can't."

"You can!"

"I can't!"

"Tell him," he said, his voice a warning. "Before it's too late."

Elena wanted to cry and scream and jump up and down like a two year old. She knew he was right, and she hated him for it. Because every second that Caroline and Stefan spent together, her chances of ever telling him how she felt dwindled lower and lower, and she knew that eventually, they would completely run out. "Fine! I'll tell him," she shouted, pulling her keys out of her pocket and clutching them in her hand firmly. "Are you happy now?"

Damon smiled smugly. "Very."

"God, I hate you," she said, pushing her way out of the bar and towards her car. His hand grabbed her arm roughly, and she twirled around to face him.

"You'll thank me one day," he murmured quietly, and before she could dwell on the fact that she was having a hard time remembering how to breathe, he dropped her arm and started walking backwards. "Good luck, coward," he chuckled, turning around and vanishing into the night.

This time, Elena did scream. She kicked the side of her car angrily before opening the door and hopping inside. She sat silently, mulling over what she was about to do in her head, before jamming the key in the ignition and pulling out of the parking lot. "Fuck it," she thought freely. Tonight had already been one of the worst nights of her life, so she might as well get this over with and add rejected by the man of her dreams to the growing list of why her life sucked.


End file.
